I focus heavily on finding insight - an accurate understanding of how things truly work together to produce certain outcomes. With insight, we can make plans based on reality (the most popular alternatives: ease, precedent, oral tradition and personal interest).
But the ultimate reality is this: we cannot plan anything with certainty. There are no guarantees, only reasonable risks and unreasonable risks.
You may be naturally risk averse, or not. It doesn't really matter. What matters is whether you are a good judge of the nature of the risk involved in a decision, and whether you are a good judge of the "reasonableness" of that risk considering the full context.
And here are two of the leader's toughest judgments of all:
* Who among my people is a good judge of risk?
* How much leeway in making risk judgments should I give that person?